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JWH 018 N-(5-hydroxypentyl) metabolite is a primary urinary metabolite of JWH 018, a synthetic cannabinoid found in several blends of the herbal mixture K2 or Spice . This biomarker is also referred to as the terminal omega hydroxy metabolite of JWH 018. It is an analytical reference standard categorized as a synthetic cannabinoid.

Mechanism of Action

Target of Action
5-OH-Jwh-018, like other synthetic cannabinoids, primarily targets the cannabinoid receptors CB1 and CB2 . These receptors are part of the endocannabinoid system, which plays a crucial role in various physiological processes such as pain sensation, mood, and memory.

Mode of Action
This compound acts as a full agonist at both the CB1 and CB2 receptors . This means it binds to these receptors and activates them, mimicking the effects of endogenous cannabinoids. The activation of CB1 receptors in the central nervous system can lead to psychoactive effects, while the activation of CB2 receptors is associated with immune response modulation .

Biochemical Pathways
For instance, JWH-018 has been shown to increase the glycolytic flux at the expense of a decrease in the pentose phosphate pathway in Saccharomyces cerevisiae

Pharmacokinetics
Synthetic cannabinoids are generally lipophilic, meaning they can easily cross cell membranes and distribute throughout the body . They are metabolized in the liver, primarily by cytochrome P450 enzymes, into various metabolites . Some of these metabolites can be more potent and longer-lasting than the parent compound .

Result of Action
The activation of cannabinoid receptors by this compound can lead to various molecular and cellular effects. For instance, it can cause changes in cell signaling, leading to effects such as sedation, cognitive dysfunction, tachycardia, postural hypotension, dry mouth, ataxia, and psychotropic effects . The exact effects can depend on factors such as the specific cell type and the individual’s genetic makeup .

Action Environment
Environmental factors can influence the action, efficacy, and stability of this compound. For instance, factors such as temperature and pH can affect the stability of the compound. Additionally, the presence of other substances (e.g., alcohol or other drugs) can influence its action and efficacy through drug-drug interactions .

Preparation Methods

Synthetic Routes and Reaction Conditions
The preparation of JWH 018 N-(5-hydroxypentyl) metabolite involves the monohydroxylation of the N-alkyl chain of JWH 018 . This process can be facilitated using physical methods such as vortex, ultrasound, or a hot water bath to aid in dissolving the compound .

Industrial Production Methods
Industrial production methods for JWH 018 N-(5-hydroxypentyl) metabolite are not extensively documented. the compound is available as a certified reference material in methanol solutions, indicating that it is produced and standardized for forensic and toxicological applications .

Chemical Reactions Analysis

Types of Reactions
JWH 018 N-(5-hydroxypentyl) metabolite undergoes various chemical reactions, including:

Oxidation: The hydroxyl group can be further oxidized to form carboxylic acids.

Glucuronidation: In urine samples, this metabolite is almost completely glucuronidated.

Common Reagents and Conditions
Common reagents used in these reactions include oxidizing agents for oxidation and glucuronic acid for glucuronidation. The reactions typically occur under physiological conditions in the human body .

Major Products Formed
The major products formed from these reactions include carboxylic acid derivatives and glucuronide conjugates .

Scientific Research Applications

Forensic and Toxicological Applications
Detection and Quantification
5-OH-JWH-018 is primarily used as an analytical reference standard in forensic and toxicological research. It aids in the detection and quantification of synthetic cannabinoids in biological samples such as urine. The compound’s unique hydroxylation at the N-alkyl chain distinguishes it from other metabolites, making it a valuable biomarker for identifying JWH-018 usage .

Immunoassays
A novel enzyme-linked immunosorbent assay (ELISA) has been developed for the detection of JWH-018 metabolites, including this compound. This assay is calibrated to detect the presence of these metabolites in urine samples, providing a reliable method for screening synthetic cannabinoid use . The assay demonstrated significant cross-reactivity with various synthetic cannabinoids, thus enhancing its utility in drug testing environments.

Pharmacological Research – Buy JWH 018 Online

Mechanism of Action
this compound acts as a full agonist at cannabinoid receptors CB1 and CB2, similar to its parent compound JWH-018. This interaction leads to various physiological effects, including alterations in cell signaling pathways that can result in sedation, cognitive dysfunction, and psychotropic effects. The compound’s pharmacokinetics indicate that it is lipophilic, allowing it to easily cross cell membranes and distribute throughout the body.

Biological Activity
Research has shown that this compound exhibits significant biological activity. It is involved in various metabolic pathways and can influence neurotransmitter release and neuronal excitability. Studies have indicated that the compound may contribute to long-term behavioral changes following administration, highlighting its potential impact on the central nervous system .

Case Studies and Research Findings
Toxicological Studies : A study involving mice demonstrated that administration of JWH-018 resulted in increased seizure activity, suggesting that its metabolites, including this compound, may have significant neurotoxic effects . This highlights the need for further research into the safety profiles of synthetic cannabinoids.
Metabolic Pathways : Investigations into the metabolic pathways of JWH-018 revealed that this compound undergoes extensive metabolism via cytochrome P450 enzymes. This metabolic process can significantly influence the pharmacokinetics and toxicity of synthetic cannabinoids .
Behavioral Impact : Repeated exposure studies indicated that synthetic cannabinoids like JWH-018 can lead to long-term changes in behavior and neurochemistry in animal models. These findings raise concerns about their potential for abuse and long-term health effects .
Comparison with Similar Compounds

Similar Compounds
JWH 018: The parent compound of JWH 018 N-(5-hydroxypentyl) metabolite.

JWH 073: Another synthetic cannabinoid with similar metabolic pathways.

AM2201: A synthetic cannabinoid with metabolites that share structural similarities with JWH 018 N-(5-hydroxypentyl) metabolite.

Uniqueness
JWH 018 N-(5-hydroxypentyl) metabolite is unique due to its specific hydroxylation at the N-alkyl chain, which distinguishes it from other metabolites of synthetic cannabinoids. This specific modification allows for its use as a biomarker in forensic and toxicological analyses .